The Tampa Tech Architect (Episode 46 ft. Tony DiBenedetto)

Most people talk about money as a motivator. Tony DiBenedetto talks about it as a mirror. Tony co-founded Tribridge in 1998 and spent nearly two decades building it into an 850-person technology firm before leading its sale to DXC Technology in 2017. He's now Chairman and CEO of Appspace, and Founder and Chair of Think Big for Kids, a national nonprofit that has helped more than 8,000 young people set and reach their post-high-school goals. He got there from a childhood spent in fifteen different homes. This conversation goes further into the formation than the résumé usually allows. Tony talks about the bagel shop he opened at 23 while working full time at Arthur Andersen — and what its failure taught him about cash flow and about his own expectations of other people. He's direct about the years before the guardrails existed: no curfew, no rules, and a proximity to real criminal activity that he neither dramatizes nor excuses. He explains why he deliberately gravitated toward partners and friends who had been raised differently, and what it took to build a filter in his twenties that most people are handed in childhood. He also names the one offer he accepted that he'd take back. "Money can affect behavior, but it also reflects character." — Tony DiBenedetto